You'll be surprised at how super easy it is for any guy to get dressed like this. Just a black overcoat paired with charcoal wool chinos. And if you wish to easily up your outfit with a pair of shoes, why not complete your ensemble with a pair of navy leather derby shoes? If you're already bored of your transitional weather style options, this outfit just might be the inspiration you need. So if you need style ideas on how to dress as you get into your 50s, this ensemble is ideal.